Réaction #1509626

Équation de réaction

2,2,2-Trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)-ethanone

2,2,2-trichloro-1-(4,5-dibromo-1-methyl-pyrrol-2-yl)-ethanone

potassium carbonate

→

title compound

Rendement 92.0%

4,5-dibromo-1-methyl-pyrrole-2-carboxylic acid methyl ester

Rendement 92.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Autrewas quenched with water (10 mL)
2. 2
   AutreThe methanol was removed under reduced pressure
3. 3
   Autrethe residue partitioned between ethyl acetate (100 mL) and water (20 mL)
4. 4
   LavageThe organic layer was subsequently washed with sat. NaHCO3 (2×30 mL), brine (2×20 mL)
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   AutreEvaporation of the filtrate

Mode opératoire

2,2,2-Trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)-ethanone 14 (1.00 g, 2.60 mmol), anhydrous potassium carbonate (0.719 g, 5.20 mmol), and anhydrous methanol (20 mL) were charged into a reaction flask. The resulting suspension was stirred for 16 h at room temperature upon which the reaction was quenched with water (10 mL). The methanol was removed under reduced pressure and the residue partitioned between ethyl acetate (100 mL) and water (20 mL). The organic layer was subsequently washed with sat. NaHCO3 (2×30 mL), brine (2×20 mL), dried over anhydrous sodium sulfate, and filtered. Evaporation of the filtrate yielded the title compound (0.710 g, 92%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 7.05 (s, 1H), 3.90 (s, 3H), 3.76 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 159.38, 123.62, 118.51, 113.93, 98.06, 51.58, 35.78; HRMS (FAB) calcd for C7H7Br2NO2 (M+) 294.8844, found 294.8861.

Source